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The movie opens with Emily kissing her scrubby looking boyfriend and they make out in front of the airport. A car parks in front of Emily's boyfriend's. Oliver gets out from the car and says a brusk goodbye to his sister. He looks at Emily and can't take his eyes off her. He sees Emily fighting with her boyfriend, and the boyfriend is being a jerk to her. They break up on the spot.
Emily and Oliver are about to board their plane. They notice each other staring. On the plane, a guy sitting in front of him abruptly pulls back his seat and a stewardess accidentally spills something on Oliver's shirt as a result. He heads to the washroom. When he is in there, someone knocks. He opens the door. It's Emily. The bathroom becomes occupied. Later, Emily walks out, with a meaningful expression on her face. A kid stares at her. Oliver also gets out a few minutes later, and sits down with a goofy smile on his face.
The two meet again at the luggage pick-up. Oliver wants to know more about her, but Emily is unwilling to be more than friends with him. They have a cute chat in the subway, but Emily isn't impressed. She leaves, and Oliver watches her from the moving streetcar.
By coincidence, Oliver notices Emily on the street across him the next day, after someone stole his jacket. (He has a colorful scarf and a hokey Oklahoma sweater on.) He quickly crosses the street and surprises her. At the same moment, Emily's parents arrive and Oliver is introduced. They seem impressed and want to take them to lunch, but Emily refuses, making up an excuse that Oliver needs to be at the hospital to get his test results back
Oliver and Emily hang out at the bar, getting to know more about each other. Oliver has set goals in his life, using analogy of "ducks in line". He wants a stable job, a house, a dream car, and then later, the woman of his dreams. Emily doesn't believe him. He writes down his number at the back of a receipt and hands it to her, saying that if in six years, he doesn't have all his ducks in line, she should pay him 50 bucks. The two spend more time, this time hanging out in the street, and Emily takes spontaneous photos of Oliver and of the scenery with Oliver's camera. The day comes to a close when Emily leaves, but stopping Oliver from saying any more.
A few years passed. Emily is no longer a hippy wannabe with black dyed hair. She is now a beautiful brunette and an aspiring actress. She makes passionate love to her boyfriend, and he tells her that the sex was great. The two seem happy, but he leaves the room to work on his laptop. Emily gets a call that tells her that she has an interview and she excitedly tells her boyfriend who looks at her with disdain. He breaks up with her. She looks disheartened.
Emily and her two friends - a brunette and a blonde - take a walk. The two girls reassure her that her breakup was a good thing. The brunette friend stops the blonde friend from giving Emily a cigarette. They also tell her that there will be a party for New Years.
Back at home, Emily calls up her past boyfriends from her address book and desperately looks for a date for the New Years party. She finds an old crumpled receipt in her address book and when she opens it, she smiles looking at Oliver's name and number. She picks up the receiver, but hesitantly drops it. Then she picks it up again and calls him. Oliver's mom answers and loudly asks Oliver to get the phone. He is surprised to hear back from Emily, who asks him out for coffee, and Oliver says that he wants to meet her at her house. Emily rinses her mouth vigorously with mouthwash before opening the door. She finds Oliver's brother, who is deaf, at her door. He says he is Oliver, but she smiles and says he isn't. Oliver comes out and says hi. The three talk, with Oliver as a jocular sign translator. Oliver's brother leaves. Emily and Oliver go in the house, and the two start making out but Emily stops him. She says that she's not the kind of girl who is desperate for sex after a breakup. They give each other a silent treatment in a restaurant (a cute scene with them having water fight), finally, Emily caves. They start getting to know more about each other.
That night, Emily gives him a shirt to wear, and she changes into a sexy dress. They arrive at the party. Emily's friends are impressed with how good looking Oliver is. Emily keeps looking at her ex and his date, while Oliver notices this and is disappointed. He excuses himself. Emily then goes over to Oliver and the two slow dance, but Emily keeps looking at her ex. She goes to the washroom. A few minutes later, the countdown to the New year starts, and she looks everywhere for Oliver but finds herself standing in front of her ex and his date making out. She is about to cry. Oliver miraculously swoops in and the two kiss. Oliver takes her to his place, but it is empty because he is moving. She is sad that he is moving when she starts liking him. She finds out that he had framed the picture she took. The two make out but Emily goes to the washroom. Oliver fixes himself, even swallowing some toothpaste, even tries a sexy pose. But he finds Emily asleep on the toilet cover. He gently carries her to a mattress and leaves. Next morning, she wakes up to find herself alone, with his shirt on to keep her warm. Oliver left her his camera.
Few more years later, we see Oliver who is now with a girlfriend. She is not happy because she thinks that Oliver is too preoccupied with work. She dumps him. Oliver is sad. He meets Emily who tries to cheer him up but he can't be moved. We find out that Emily became a photographer. The two take a spontaneous road trip. They make out, and take a naked picture together under the moon. But this time, Oliver has an important meeting for his business and he has to leave. While he is there, Emily asks him to visit her mother's grave. He and she talk on the phone, while he cheers her up about having lost her mother young. She thanks him.
Oliver makes a painful decision between Los Angeles and San Francisco. He wants to stay with Emily but has to move in order to make his business successful. He moves. His business booms. But a few years later, it is closed down. Oliver returns to his parents' house full of emotion. His brother encourages him to live his life instead of being caught up on goals. One day, he finds Emily's work displayed in front of a store. After hearing that the artist comes by often, he waits for her to come from across the street. He bumps into her again, at last. This time, he has a guitar and sings her a song in front of her house. He then tells her that he doesn't have a stable job, he has neither a house nor a car, but could she marry him? She is however already engaged. The two part again, but look at each other longingly.
Few months later, Emily is still engaged, but realizes that she doesn't love her fiance. She breaks up her engagement. She looks up Oliver, but all the while, having heard from her brunette friend that he is about to be married. She goes to his house. He immediately notices her, she looks back at him, embarrassed. When Oliver quickly runs to her, she tries to run away but hits her head on the glass door. Everyone crowds around her, and urges Oliver to go back to the wedding. But Oliver helps Emily get up and asks her what she is doing at his place. She says that she looked him up. She then says that she should leave, her teary eyes looking back at him. Everyone at the wedding is staring at him, and he is staring at Emily who leaves. He looks in Emily's direction, at the party, and then back at where Emily was. He quickly runs to catch her. When she is walking to her car, he stops her. Everyone from the party followed him. It turns out that it was his sisters' wedding, not his. Emily and Oliver laugh. They kiss.
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